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After becoming the boss of the Chicago Outfit in 1957, 49 year old Sam Mooney Giancana was living like royalty. He had a beautiful house, several luxury cars and a collection of exotic antiques. He took lavish trips to Mafia owned casinos in Las Vegas, where he palled around with celebrities like Frank Sinatra and Marilyn Monroe. It was exciting to be around such big stars, but Sam had his eyes set even higher on the world of politics, specifically on an ambitious young senator named John F. Kennedy. Frank Sinatra introduced Sam to Kennedy in 1959 when the politician was gearing up to run for president. Sam liked jfk. They were both hard drinkers and big womanizers, but more than that, Sam really liked the idea of having the ear of the President of the United States. So Sam decided to throw the full weight of the Chicago outfit behind Kennedy's campaign against Richard Nixon on November 8, 1960. The election was too close to call. Democratic strongholds like Ohio, Kentucky and Tennessee had unexpectedly gone for Nixon, leaving the race nearly tied. As votes were tallied, it became clear that whoever won Illinois would be the next president. Luckily for John F. Kennedy, Sam Giancana had done more for his campaign than just donate money. On Election Day, Sam's men drove groups of voters from one polling precinct to another so they could vote multiple times. In some neighborhoods, Sam's thugs stood outside reminding voters that Sam expected them to back Kennedy. After all the votes were counted, Kennedy carried Illinois by just 9,000 votes and became the 35th president of the United States. As a boy, Sam Giancana had brawled with Irish kids for control of the Patch. Now he'd just helped put the first Irish Catholic president into the White House. And Sam expected Kennedy to return the favor by looking the other way when it came to the Chicago outfit. But Kennedy ran a hard bargain. Before agreeing to anything, he allegedly needed something from Sam. And it was a pretty big ask. Apparently he wanted Sam to help the CIA kill Cuban dictator Fidel Castro. While the CIA had been gathering intelligence on Castro for years, they hadn't been ready to actually take him down. But now with Sam on their side, the Kennedy administration thought they might have the missing piece. They figured a kingpin like Sam would know plenty of cold blooded killers who could help them get the job done. Sam passed along the name of one of his operatives to the CIA. A wildly corrupt Chicago cop named Richard Kane who was fluent in five languages and an expert marksman. Soon the CIA was putting Cain to work training Cuban exiles to overthrow Castro's government. By 1961, the invasion was all planned and the Cuban soldiers were ready to go. But there were some unexpected bumps along the way. On April 14, 1961, a brigade of 1400 CIA backed Cuban exiles and mercenaries landed at Cuba's Bay of Pigs. But before they even got inland, they were quickly defeated by Castro's army. The failed Bay of Pigs invasion was a massive embarrassment for the Kennedy administration. Privately, JFK blamed the CIA for bungling the operation and fired several key members of the agency in retaliation. The CIA agents Sam had worked with were furious at Kennedy, who they believed had stabbed them in the back. Seeing how Kennedy double crossed his own spies, Sam grew concerned. If the President was willing to turn on his own operatives, how could Sam trust him to keep his promise and stay away from the Chicago mob? Sam was right to question Kennedy's loyalty. Over the next couple of years, the President's brother, Attorney General Robert F. Kennedy, established a special organized crime task force. Soon FBI agents were aggressively surveilling the Chicago outfit's operations. Sam tried to get in touch with JFK for an explanation, but none of his White House contacts were returning his calls. Sam's troubled relationship with the president ended on November 22, 1963 when Kennedy was gunned down by Lee Harvey Oswald in Dallas, Texas. In the decades since, rumors have swirled that Sam Giancana had teamed up with the disgruntled ex CIA operatives to orchestrate Kennedy's assassination as revenge. However, while declassified documents have confirmed confirmed Sam's involvement with the CIA's Cuba operations, there's no evidence he was involved in Kennedy's murder. But even though JFK was Gone. The FBI was still watching the Chicago outfit around the clock. And in 1965 they started to take action. That year, 57 year old Sam was served with a subpoena to testify at a grand jury hearing on organized crime. He ignored it and spent a year in jail for contempt of court. Sam had obeyed the Mafia's golden rule, never talk to the police. But if he was hoping his fellow gangsters would appreciate his silence, he was sorely mistaken. Shortly after his release in 1966, Sam's lieutenants in the Chicago outfit let him know he had too much heat on him. He was a magnet for attention and it was having a serious impact on the outfit's bottom line. It was a polite suggestion, but Sam had spent enough time in the mob to know what would happen if he didn't take the hint. So in 1967, 59 year old Sam Giancana retired as head of the Chicago outfit. Right after he moved to Mexico, where he hoped to avoid any mobsters or government agents who had unfinished business with him. The but just because he wasn't in the US didn't mean he was in the clear. In July 1974, after seven years in the tropical city of Cuernavaca, 66 year old Sam was arrested by Mexican police. He'd overstayed his tourist visa and was deported back to the United States. There he resettled in a bungalow in the wealthy Chicago suburb of Oak Oak Park. By then, Sam's health was failing. He was suffering from a gallbladder disorder and had multiple operations over the course of the next year. In the middle of all this, he got some unexpected News. In early 1975, Sam received another subpoena, this one from the US Senate's Church Committee. Headed by Idaho Senator Frank Church, the committee was tasked with investigating abuses and corruption within the US Intelligence community. Because Sam had firsthand knowledge that the government had worked with organized crime figures like himself, the Church committee was eager for him to testify. The last time Sam had gotten a subpoena like this one, he'd ignored it and ended up in prison. Now Sam was very sick. He knew his days were numbered and he didn't want to spend whatever time he had left behind bars. So he agreed. But just days before he was scheduled to testify, somebody silenced Sam Giancana for good. On the night of June 19, 1975, Sam's caretaker found him dead on the floor of his kitchen. Shot six times in the head. He was 67 years old. He was the first person in US history who was killed to prevent them from testifying before Congress. Sam Giancana's murderer was never caught. Some people believed he was killed by the Chicago outfit, while others think it was a former CIA operative who wanted to protect the Agency's reputation. We'll probably never know the truth, but not even a bullet could change the fact that the little Italian runaway had left a lasting impression on Chicago and America. Coming up, another history making mobster who met a mysterious end 28 years before Sam Giancano was gunned down in his home by an unknown assailant. Another mob kingpin met a similar fate. Like Sam, this mafioso started his criminal career as a young boy before rising in the ranks to to rub elbows with America's elite. Along the way, he turned a desolate desert town into one of the world's hottest tourist attractions. On the evening of June 20, 1947, 41 year old Benjamin Bugsy Siegel was enjoying a quiet night at his Beverly Hills mansion. Bugsy was one of America's most famous gangsters. He was a founding member of the mafia run assassin ring Murder Inc. A friend to Hollywood superstars like Cary Grant, and the owner of Las Vegas newest casino. Needless to say, he had a lot going on. He probably felt like he'd earned a little rest and relaxation. At around 10:30pm Bugsy was lounging on the couch reading the Los Angeles Times when nine bullets crashed through the living room window. The first round hit Bugsy square in the head. Three other shots hit him in the face and chest. But the job was already done. The former chairman of Murder Inc. Had just been killed himself. In some ways, he was the victim of his own success. But he was also undoubtedly the victim of his failures. Benjamin Siegel's life began on the other side of the country in a Brooklyn tenement on February 28, 1906. He was one of five children whose parents were poor Jewish immigrants from Eastern Europe. While his mother stayed home with the kids, Benjamin's dad spent his days making clothes in a sweatshop. Barely earning enough to keep food on the table for his family. Benjamin saw how hard he worked to make so little and he decided at an early age that he didn't want to follow in his father's footsteps. By the time he was 12 in 1918, Benjamin had given up on school to focus on a much more lucrative pastime. He and his friends would walk up to streetcar vendors in their neighborhood and ask for a dollar. If the vendor said no, the boys would say splash kerosene on the vendor's goods, then set them on fire. The next time they came back around, the vendor knew to give them the money. In the world of organized crime, this is called a protection racket. And Benjamin was very good at it. Soon he became known as Bugsy for his short temper and tendency to go bugs, a slang term for lashing out with acts of ferocious violence. Before long, Bugsy's antics caught the eye of another streetwise hooligan from a Jewish family, Meyer Lansky. Meyer was four years older than Bugsy and was inspired by New York's Irish and Italian street gangs. He wanted to create one for Jewish kids like him and he wanted Bugsy to be his first recruit. Bugsy was all in. Soon they were recruiting the more and more Jewish boys to their cause. Eventually, locals began calling their operation the Bugs and Meer Mob. Over the next 10 years, the bugs and Meer Mob expanded from a simple street gang to the beginnings of a criminal empire. They ran illegal card games, extorted protection money from businesses all over Brooklyn and stuff. Staged daring robberies in Manhattan and Harlem. Hot headed Bugsy was the gang's chief enforcer. If you owed the gang money from a card game or were behind on your protection payments, Bugsy would be the one to smack you around until you paid up. Meanwhile, Meyer was the brains of the operation, running the business, counting the money, always strategizing and thinking about the big picture. It was this long term thinking that led Meyer to forge an alliance with a young Italian American gangster named Charles Lucky Luciano. While most Sicilian mafiosos looked down on the still up and coming the Bugs and Meyer mob, Lucky Luciano respected their hustle. The two gangs coordinated with one another, peacefully divvying up neighborhoods to maximize profits and minimize unnecessary violence. These young criminals were taking a more businesslike approach to organized crime than the older, more traditional Sicilian gang bosses. And it wasn't long until their efforts paid off. For the next decade, Bugsy, Meyer and Lucky worked together to take down New York's more established gangs. The city's most powerful gangster, Joe Masseria, head of the Genovese crime family, was wrapped up in a massive turf war with a rival Italian gang. Bugsy and his cronies saw this and sensed an opportunity. While Joe Masserio was focused on an endless cycle of assassinations, the Bugs and Meyer mob was steadily muscling in on his bootlegging empire. Although Bugsy and Meyer were busy growing their criminal enterprise, they still felt found time for romance. And like everything else in their lives, they did it together. In 1927, they started double Dating a pair of girls from the Lower east side, Esta Krakauer and Anna Citron, Bugsy's girlfriend. Esta was crazy about him and the two got married in 1929 when Bugsy was 22 and she was 17. Meyer and Anna followed suit for four months later. And while both women knew their husbands were involved with bootlegging, neither was aware of how deadly their business was or how much more violent it was about to get. On April 15, 1931, a new era in organized crime began. That night, Lucky Luciano invited Joe Masseria to dinner and an attempt Italian restaurant in Coney Island. He said he wanted to talk about forming an alliance. After a few hours of whining and dining, Joe Lucky excused himself and went to the bathroom. Moments later, Bugsy Siegel rushed in with three of his most trusted killers and shot Joe dead at the dinner table. With that, the old guard was officially finished. Now 25 year old Bugsy Siegel, 29 year old Meyer Lansky and their ally, 34 year old Lucky Luciano, were the most powerful gangsters in New York. Together they joined forces to form a new criminal organization. One that finally united Italian, Irish and Jewish criminals in pursuit of profit. They called themselves the Syndicate. The Syndicate did all the things the Bugs and Meyer mob used to do. Protection rackets, illegal gambling, bootlegging, robbery. But on a much bigger scale. The group expanded out of New York and into cities all over the East Coast. The Syndicate was run by a commission which included all the most important gang leaders on the East Coast. This commission mediated disputes and voted on the Syndicate's operations, ensuring that disagreements were handled in the boardroom instead of on the streets. Bugsy ran the Syndicate's enforcement arm, chillingly known as Murder, Inc. If the commission voted that someone needed to die, Murder Inc. Would do the dirty work. Bugsy recruited and trained a small army of hitmen who killed up to a thousand people during the 1930s. He joined in on the violence whenever he could. But one day in the fall of 1932, the violence came looking for him. Bugsy was driving to a meeting with a business associate in Manhattan when a car pulled up beside him at a red light. Moments later, the passengers in the other vehicle pointed a machine gun at Bugsy and fired. Bugsy's car was bulletproof and he managed to speed off unharmed. Afterward, he returned to his and Meyer's hideout on Grand Street. And then. That's when a bomb went off. It had been stashed in the chimney. Although his injuries were minor, Bugsy's men rushed him to the hospital. And while he'd escaped with his life, Bugsy was furious. Through his underworld sources, he learned the attempted hits had been ordered by a gangster named Tony Fabrazzo. Bugsy and his Murder Inc. Hitmen had killed two of Tony's brothers for messing with the syndicate. Tony had wanted to avenge their deaths. Now Bugsy was eager to even the score. A few nights after the bombing, Bugsy told his nurses at the hospital that he was going to bed early. He hid a few pillows under his blankets, then snuck out of the first floor window where his men were waiting in a car to whisk him away. Bugsy knew Tony was hiding out at his dad's house until the heat died down. His men drove him over, and Bugsy knocked on the door. When Tony's elderly father answered, Siegel flashed a fake badge and claimed to be a detective. With some questions from Mr. Fabrazzo's son. The old man summoned Tony to the front door. As soon as he appeared, Bugsy drew his gun and shot Tony Tony in the face while his family watched. Then he hurried back to the hospital. He climbed back through the window and into his bed. If the police came calling about the murder, the nurses could back up his alibi. He'd been asleep all night. But even though he'd outmaneuvered the law, Bugsy's brazen killing caused a lot of headaches for Meyer Lansky and the rest of the city syndicate. It hadn't been approved by the commission and generated headlines and publicity that the syndicate didn't want. To make things even worse, New York City's newly elected mayor, anti corruption crusader Fiorello laguardia had pledged to crack down on organized crime. With this much heat on them, the syndicate needed to play it cool and keep a low profile. But everyone on the commission knew that playing it cool wasn't exactly Bugsy's strong suit. So they hatched a plan to keep their hot headed enforcer as far away from their New York operations as possible. In 1933, Bugsy Siegel took his first trip out to Los Angeles. The syndicate had decided to open a West coast operation. And they thought he was the perfect man for the job.